Metal-free addition of aliphatic carboxylic acids to cyanopropargyl alcohols: an access to new families of functionalized dihydrofurans and 3(2H)-furanones

Olesya A Shemyakina,Boris A Trofimov,Anton V Stepanov,Viktoria V Kireeva,Anastasiya G Malkina,Olga G Volostnykh,Konstantin A Apartsin,Igor A Ushakov

doi:10.24820/ark.5550190.p010.569

Olesya A Shemyakina, Boris A Trofimov + Show 6 more

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https://doi.org/10.24820/ark.5550190.p010.569

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Abstract

Metal-free addition of aliphatic carboxylic acids to cyanopropargyl alcohols: an access to new families of functionalized dihydrofurans and 3(2H)-furanones

Highlights

IntroductionFunctionalized derivatives of dihydrofurans are currently in focus of synthetic organic chemistry.[1,2,3] These structures are closely related to the ribose fragment of nucleosides, DNA and other ribosetailored life-sustaining structures including diverse dehydro and deoxy sugars.[4,5,6] Dihydrofuran scaffold is frequently met in natural products and pharmaceuticals.[7,8,9] As a typical illustration, 2,3-dihydrofuran ring is a fragment of diterpenoids (bicunningine A and B), isolated from a tree of traditional Chinese medicine used for the treatment of hernia, arthritis and strangury.[10] Dihydrofuran derivatives are widely employed as versatile building blocks in synthetic organic chemistry.11 2,3-Dihydrofurans are recognized as precursors for the asymmetric synthesis of tetrahydrofurans.[12,13,14,15,16] Synthetic approaches to 2,3-dihydrofurans involve the [4+1] cycloaddition of enones with diazo compounds,[17,18] the [3+2] cyclization of aldehydes with β-ketosulfides/βketosulfones.[11,19,20,21] For this purpose, the ring closing reaction of 1,3-dicarbonyl compounds with alkenes is efficient as well.[22,23,24,25] Cyclization of the but-3-yn-1-ols is a method of choice for the synthesis of 2,3dihydrofurans.[26,27,28,29] Recently, a method for the preparation of functionalized 2,3-dihydrofurans by Sc(OTf)3catalyzed cyclization of α-allylated 1,3-dicarbonyl compounds has been reported.[11] The palladium-catalyzed reaction of aryl and heteroaryl bromides, chlorides, and nonaflates with α-allyl-β-ketoesters provides a ready access to functionalized 2,3-dihydrofurans.[30]
Functionalized derivatives of dihydrofurans are currently in focus of synthetic organic chemistry.[1,2,3] These structures are closely related to the ribose fragment of nucleosides, DNA and other ribosetailored life-sustaining structures including diverse dehydro and deoxy sugars.[4,5,6] Dihydrofuran scaffold is frequently met in natural products and pharmaceuticals.[7,8,9] As a typical illustration, 2,3-dihydrofuran ring is a fragment of diterpenoids, isolated from a tree of traditional Chinese medicine used for the treatment of hernia, arthritis and strangury.[10]
Dihydrofuran derivatives are widely employed as versatile building blocks in synthetic organic chemistry.11 2,3-Dihydrofurans are recognized as precursors for the asymmetric synthesis of tetrahydrofurans.[12,13,14,15,16]

Summary

Introduction

Functionalized derivatives of dihydrofurans are currently in focus of synthetic organic chemistry.[1,2,3] These structures are closely related to the ribose fragment of nucleosides, DNA and other ribosetailored life-sustaining structures including diverse dehydro and deoxy sugars.[4,5,6] Dihydrofuran scaffold is frequently met in natural products and pharmaceuticals.[7,8,9] As a typical illustration, 2,3-dihydrofuran ring is a fragment of diterpenoids (bicunningine A and B), isolated from a tree of traditional Chinese medicine used for the treatment of hernia, arthritis and strangury.[10] Dihydrofuran derivatives are widely employed as versatile building blocks in synthetic organic chemistry.11 2,3-Dihydrofurans are recognized as precursors for the asymmetric synthesis of tetrahydrofurans.[12,13,14,15,16] Synthetic approaches to 2,3-dihydrofurans involve the [4+1] cycloaddition of enones with diazo compounds,[17,18] the [3+2] cyclization of aldehydes with β-ketosulfides/βketosulfones.[11,19,20,21] For this purpose, the ring closing reaction of 1,3-dicarbonyl compounds with alkenes is efficient as well.[22,23,24,25] Cyclization of the but-3-yn-1-ols is a method of choice for the synthesis of 2,3dihydrofurans.[26,27,28,29] Recently, a method for the preparation of functionalized 2,3-dihydrofurans by Sc(OTf)3catalyzed cyclization of α-allylated 1,3-dicarbonyl compounds has been reported.[11] The palladium-catalyzed reaction of aryl and heteroaryl bromides, chlorides, and nonaflates with α-allyl-β-ketoesters provides a ready access to functionalized 2,3-dihydrofurans.[30]

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